Every business has a “Jay.” They’re the customer who takes up more time than anyone else, wants “just one more thing” after every deliverable, and somehow turns a profitable project into a drain on your energy and your team.
This is your weekly Entrepreneur Insights 5-minute read with ideas to improve your business in a How to series format.
A Jay customer is one who can be difficult, overly demanding or sometimes obnoxious.
You can’t build a healthy business by avoiding Jays entirely. But you also can’t let them set the rules. Here’s how to handle them strategically.
1. Diagnose the real problem
Most Jay customers aren’t trying to be difficult. They’re anxious.
They worry about wasting money, looking bad to their boss or partner, or choosing the wrong strategy. That anxiety shows up as micromanaging, endless questions, and scope creep.
Before you react to the behaviour, identify the underlying fear. Ask: “What would make this feel like a win for you?” and “What would you be worried about if this didn’t work?” Their answers give you a real brief.
2. Tighten expectations in writing
Jay customers thrive in ambiguity. You don’t.
Turn vague agreements into specifics:
- Clear deliverables
- Timelines with milestones
- Revision limits and response windows
- What’s included, and what triggers an extra fee
You’re not being rigid. You’re protecting both sides from confusion. The more concrete the agreement, the fewer emotional debates you’ll have later.
3. Lead the communication cadence
If you wait for a Jay customer to reach out, they’ll do it constantly and at random.
Preempt that by setting a communication rhythm: “You’ll get an update from me every Thursday by noon. If anything urgent comes up, I’ll let you know earlier.”
Regular, proactive updates calm anxious customers and dramatically reduce “checking in” messages.
4. Use boundaries as a value signal
Boundaries aren’t just self-care. They’re a positioning tool.
When you say, “This is outside our original scope; here’s the add-on fee,” you’re sending a message: you run a professional operation with a defined process. Serious clients respect that. Chronic Jays often don’t, which tells you everything you need to know.
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5. Decide if the relationship is worth it
Finally, not every Jay should be “fixed.”
If a customer ignores boundaries, disrespects your team, or brings in more stress than revenue, your job as an entrepreneur is to say “no.” Let them go and make room for customers who value your work. Sometimes, they cannot become profitable for you.
You can’t eliminate Jay customers. But with clear expectations, strong boundaries, and proactive communication, you can turn many of them from chaos engines into steady, profitable accounts.
Quote for the week
“Customer service shouldn’t just be a department; it should be the entire company.”—Tony Hsiehm, founder of Zappos.
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See you next week for another edition of weekly Entrepreneur Insights. May you always have the mindset of an entrepreneur.
Sajjad Hamid is an SME & Family Business Adviser who supports entrepreneurs in scaling their ventures. In his spare time in Trinidad and Tobago, he cultivates organic tropical fruits and vegetables, practising sustainable farming in his home garden.
He is the author of Build Your Legacy Business: Solopreneur To Family Business Hero. Sajjad is a Fellow of the Family Firm Institute. He writes a column titled Entreprenomics in the Business section of the Trinidad and Tobago Guardian. You can contact him at [email protected] or visit www.entrepreneurtnt.com.
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